1. Field of the Invention
This invention relates to an antibody capable of undergoing specific linkage with a pyrethroid compound, a novel compound useful as a hapten for the preparation of the antibody (which may hereinafter be called a "haptenic compound"), a novel compound useful as an intermediate for the synthesis of the haptenic compound, an immunogen composed of the haptenic compound, and preparation processes thereof; and a method for the detection and measurement of one or more pyrethroid compounds in a sample by the use of the antibody.
2. Description of the Related Art
As immunochemical analyses of pyrethroid compounds, there are "Study on Antibodies specific to S-Bioallethrin" [J. Agric. Food Chem., 26, 1328-1333(1978)] and "Radioimmunoassay" [Experimentia, 35, 1619-1620(1679)], both reported by B. D. Hammock et al. These are fundamental studies on the application of an immunochemical analysis to a specific pyrethroid.
There is also a report by L. H. Stanker et al. of a basic study on the immunochemical analysis of permethrin in meat [J. Agric. Food Chem., 37, 834-839(1989)]. According to the report, three monoclonal antibodies were isolated by oxidizing dimethylvinyl groups of phenothrin with ozone into a carboxylic acid derivative, binding the derivative with a protein to obtain a hapten-protein conjugate and immunizing a responder with the conjugate. These antibodies, how ever, are only useful for the detection of phenothrin, permethrin, cypermethrin and deltamethrin and have very low detection sensitivity to other synthetic pyrethoids. When an antibody is reacted to a compound to be detected, a water-soluble organic solvent such as acetonitrile is added to increase the solubility of the compound in a sample so that the compound is rendered more reactive. In consideration of the stability of the antibody against the organic solvent, the concentration of the solvent must be controlled low, that is, at 6% or lower, leading to the unresolved problems that compounds having extremely low water solubility can hardly be detected and solvent removal or concentration is indispensable similarly to other microanalyses.
There is a growing social concern with the problem of pesticide residue in our living environment, particularly, with the ever increasing problem of post harvest application of pesticides in imported foods. In order to secure the safety of the living environment, it is necessary to precisely and promptly measure the amount of each pesticide remaining in a number of samples from the environment and foods.
Pesticide residues have heretofore been measured primarily by gas chromatography or high-performance liquid chromatography. These methods, however, are accompanied with such drawbacks that they require considerable labor and time for the preparation of a sample for analysis and measuring instruments, reagents and the like are costly. There is accordingly a desire for the development of a new, easy, economical and quick measuring method.
Pyrethroid compounds, which are targets of the analysis according to the present invention, are general-purpose insecticides having a wide spectrum so that they have been used widely for the control of sanitary insects found in grain, fruits, vegetables, cotton, coffee beans, tea leaves, animals, woods and home. The application field of pyrethroid compounds has been widening because of their lower toxicity against mammary animals and stronger effects for the control of insecticide-resistant insects compared with many other insecticides. The pyrethroid compounds each has a legally-imposed permissible upper limit on its residual amount in most foods. In addition, many pyrethroid compounds have strong toxicity against aquatic animals so that their influence to the environment is worried.